There is a movie from 1996 that touches on transgender dating; an interesting subject to explore someday.
If anyone ever had any doubt that a male (transgender or not) could play and carry a feature movie playing a female lead, they need look no further than the 1996 movie, "Different for Girls". Here is the summary from IMBd.
Karl Foyle and Paul Prentice were best mates at school in the Seventies. But when they meet again in present-day London things are definitely not the same. Karl is now Kim, a transsexual, and she has no desire to stir up the past while she's busy forging a neat and orderly new life. Prentice, on the other hand, has charm but is a social disaster stuck in a dead-end job. His main talent is for getting them both into trouble. Amid the squabbles, they start to fall in love. One night, Kim invites Prentice to a romantic dinner at her flat. Prentice, finding the seduction unexpectedly effective, freaks out. He proceeds to make a public display of both of them and winds up in court. Humiliated and angry, Kim runs away. Only she can save Prentice now, but will true love triumph for a new made woman and an aging punk?
The lead character, Kim, is convincing, sincere, and wins our hearts. Her goal is to just live her life until Prentice disrupts everything.
The full movies is available on YouTube - Enjoy.